Herbicidal substituted benzoylpyrazoles

ABSTRACT

The invention relates to benzoylpyrazoles of the general formula (I), 
                         
in which Q, R 1 , R 2 , R 3 , R 4 , R 5 , Y and Z are as defined in the disclosure, to processes and intermediates for their preparation, and to their use as herbicides.

The present patent application has been filed under 35 U.S.C. 371 as anational stage application of PCT/EP02/05046, filed May 8, 2003, whichwas published in German as International Patent Publication WO02/094,792 on Nov. 28, 2002, which is entitled to the right of priorityof German Patent Applications 101 24 578.5, filed May 21, 2001, and 10138 577.3, filed Aug. 6, 2001.

The invention relates to novel substituted benzoylpyrazoles, to aprocess for their preparation and to their use as herbicides.

It is already known that certain substituted benzoylpyrazoles, such asthe compounds N-[2,6-dichloro-3-[(5-hydroxy- 1-methyl-1H-pyrazol-4-yl)-carbonyl]-phenyl]-acetamide,[2,6-dichloro-3-[(5-hydroxy- 1-methyl-1H-pyrazol-4-yl)-carbonyl]-phenyl]-carbamic acid methyl ester,N′-[2,6-dichloro-3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-phenyl]-N,N-diethyl-urea,[2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-carbamicacid methyl ester, N′-[2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-N,N-diethyl-urea,N-[3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-acetamide,N-[3-[(5-hydroxy- 1-methyl-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-propanamide,N-[3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-acetamide,N′-[2-chloro-3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-6-methyl-sulphonyl-phenyl]-N,N-diethyl-urea,N-[3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-formamide,[3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-carbamicacid methyl ester,N-[2-chloro-3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-acetamide,N-[2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-acetamide,N-[3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-2,2,2-trifluoro-acetamide,N-[3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-2,2,2-trifluoro-acetamide,N-[3-[(5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-2-methyl-6-methylsulphonyl-phenyl]-N-methyl-formamide,N-[2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-N-methyl-carbamicacid methyl ester,N-[2-chloro-3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-6-methylsulphonyl-phenyl]-N,N′-diethyl-N-methyl-urea andN-[2,6-dichloro-3-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-phenyl]-N-methyl-carbamicacid methyl ester (cf. JP-A-11292849—cited in Chem. Abstracts131:286507) have herbicidal properties (cf. also EP-A-352543, U.S. Pat.No. 5,846,907, WO-A-96/26206, WO-A-97/41105, WO-A-97/41116,WO-A-97/41117, WO-A-97/41118, WO-A-97/46530, WO-A-98/28981,WO-A-98/31681, WO-A-98/31682, WO-A-99/07697, WO-A-99/10328,WO-A-00/58306). However, the activity of these compounds is not entirelysatisfactory.

This invention, accordingly, provides the novel substitutedbenzoylpyrazoles of the general formula (I)

in which

-   Q represents O (oxygen) or S (sulphur),-   R¹ represents in each case optionally substituted alkyl, alkenyl,    alkinyl or cycloalkyl,-   R² represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or    represents in each case optionally substituted alkyl, alkoxy,    alkylthio, alkoxycarbonyl or cycloalkyl,-   R³, R⁴ independently of one another represent hydrogen, nitro,    cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or in each case    optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl,    alkylsulphonyl, alkylamino, dialkylamino, dialkylaminocarbonyl or    dialkylaminosulphonyl,-   R⁵ represents hydrogen or represents in each case optionally    substituted alkyl, alkoxy, alkylthio, alkylsulphinyl,    alkylsulphonyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl,    arylthio, arylsulphinyl, arylsulphonyl, arylalkyl, or represents the    grouping —C(Q)-Z,-   Y represents hydrogen or in each case optionally substituted alkyl,    alkylsulphonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl,    dialkylaminocarbonyl, alkenyl, alkenylsulphonyl, alkenylcarbonyl,    alkinyl, alkinylcarbonyl, cycloalkyl, cycloalkylcarbonyl,    cycloalkylalkyl, phenyl, phenylsulphonyl, phenylcarbonyl,    phenylalkyl, phenylalkylsulphonyl, phenylalkylcarbonyl or    phenylcarbonylalkyl, and-   Z represents amino, cyanoamino, nitroamino, hydroxyamino, hydrazino,    -   represents in each case cyano-, alkoxy-, alkylthio-,        alkylsulphinyl- or alkylsulphonyl-substituted alkyl, alkoxy,        alkylthio or alkylamino,    -   represents in each case optionally substituted alkylcarbonyl,        alkoxycarbonyl, alkoxyamino, alkylhydrazino,        alkylcarbonylhydrazino, alkoxycarbonylhydrazino,        alkylsulphonylhydrazino, N-alkyl-alkoxyamino, dialkylhydrazino,        alkenyloxy, alkenylamino, alkenyloxyamino, aLkinyloxy,        alkinylamino, cycloalkyl, cycloalkyloxy, cycloalkylamino,        cycloalkylhydrazino, cycloalkylalkyl, cycloalkylalkoxy,        cycloalkylalkylamino, aryl, arylcarbonyl, aryloxy,        aryloxycarbonyl, arylthio, arylamino, arylhydrazino, arylalkyl,        arylalkoxy, arylalkylthio, arylalkylamino, heterocyclyl,        heterocyclyloxy, heterocyclylthio, heterocyclylamino, the        grouping —N=(heterocyclyl), heterocyclylalkyl,        heterocyclylalkoxy, heterocyclylalkylthio or        heterocyclylalkylamino,    -   including all possible tautomeric forms of the compounds of the        general formula (I) and the possible salts of the compounds of        the general formula (I).

Preferred meanings of the radicals or groupings present in the formulaegiven above and below are defined below.

-   Q preferably represents O.-   R¹ preferably represents optionally cyano-, halogen-, C₁-C₄-alkoxy-,    C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-    substituted alkyl having 1 to 6 carbon atoms, represents in each    case optionally cyano- or halogen-substituted alkenyl or alkinyl    having in each case 2 to 6 carbon atoms, or represents optionally    cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 6    carbon atoms.-   R² preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl,    halogen, represents in each case optionally cyano-, halogen- or    C₁-C₄-alkoxy-substituted alkyl, alkoxy or alkoxycarbonyl having in    each case up to 6 carbon atoms, represents optionally    halogen-substituted alkylthio having 1 to 6 carbon atoms, or    represents optionally cyano-, halogen- or C₁-C₄-alkyl-substituted    cycloalkyl having 3 to 6 carbon atoms.-   R³, R⁴ independently of one another preferably represent hydrogen,    nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, represent    in each case optionally halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,    C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl,    alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each    case up to 4 carbon atoms in the alkyl groups, or represent    alkylamino, dialkylamino, dialkylaminocarbonyl or    dialkylaminosulphonyl having in each case up to 4 carbon atoms in    the alkyl groups.-   R⁵ preferably represents hydrogen, represents in each case    optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl,    alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl having in each    case 1 to 6 carbon atoms in the alkyl groups, represents in each    case optionally cyano- or halogen-substituted alkenyl or alkinyl    having in each case 3 to 6 carbon atoms in the alkenyl and alkinyl    groups, respectively, represents in each case optionally cyano-,    halogen- or C₁-C₄-alkyl-substituted cycloalkyl or cycloalkylalkyl    having in each case 3 to 6 carbon atoms in the cycloalkyl groups    and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,    represents in each case optionally nitro- cyano-, C₁-C₄-alkyl-,    C₁-C₄-halogenalkyl-, C₁-C₄-alkoxy-, C₁-C₄-halogenalkoxy-,    C₁-C₄-alkylthio-, C₁-C₄-halogenalkylthio-, C₁-C₄-alkylsulphinyl-,    C₁-C₄-halogenalkylsulphinyl-, C₁-C₄-alkylsulphonyl- or    C₁-C₄-halogenalkyl-sulphonyl-substituted aryl, arylthio,    arylsulphinyl, arylsulphonyl or arylalkyl having in each case 6 or    10 carbon atoms in the aryl groups and, if appropriate, 1 to 4    carbon atoms in the alkyl moiety, or represents the grouping    —C(Q)-Z.-   Y preferably represents hydrogen, represents optionally cyano-,    carbamoyl-, halogen-, C₁-C₄-alkoxy- or    C₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms,    represents optionally halogen-substituted alkylsulphonyl having 1 to    6 carbon atoms, represents in each case optionally cyano-, halogen-    or C₁-C₄-alkoxy-substituted alkylcarbonyl, alkoxycarbonyl or    alkylaminocarbonyl having in each case 1 to 6 carbon atoms in the    alkyl groups, represents dialkylaminocarbonyl having 1 to 4 carbon    atoms in the alkyl groups, represents in each case optionally cyano-    or halogen-substituted alkenyl, alkenylcarbonyl, alkinyl or    alkinylcarbonyl having in each case up to 6 carbon atoms, represents    optionally halogen-substituted alkenylsulphonyl having up to 6    carbon atoms, represents in each case optionally cyano-, halogen- or    C₁-C₄-alkyl-substituted cycloalkyl, cycloalkylcarbonyl or    cycloalkylalkyl having in each case 3 to 6 carbon atoms in the    cycloalkyl groups and, if appropriate, 1 to 3 carbon atoms in the    alkyl moiety, or represents in each case optionally nitro-, cyano-,    carbamoyl-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenalkyl-,    C₁-C₄-alkoxy- or C₁-C₄-halogenalkoxy-substituted phenyl,    phenylsulphonyl, phenylcarbonyl, phenyl-C₁-C₄-alkyl,    phenyl-C₁-C₄-alkyl-sulphonyl, phenyl-C₁-C₄-alkyl-carbonyl or    phenylcarbonyl-C₁-C₄-alkyl.-   Z preferably represents amino, cyanoamino, nitroamino, hydroxyamino,    hydrazino,    -   represents in each case cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,        C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl,        alkoxy, alkylthio or alkylamino having in each case 1 to 6        carbon atoms, represents C₁-C₄-alkylcarbonyl or        C₁-C₄-alkoxycarbonyl,    -   represents in each case optionally cyano-, halogen-,        C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- or        C₁-C₄-alkylsulphonyl-substituted alkoxyamino, alkylhydrazino,        alkylcarbonylhydrazino, alkoxycarbonylhydrazino or        alkylsulphonylhydrazino having in each case 1 to 6 carbon atoms        in the alkyl groups, represents N-alkyl-alkoxyamino or        dialkylhydrazino having in each case 1 to 4 carbon atoms in the        alkyl groups,    -   represents in each case optionally halogen-substituted        alkenyloxy, alkenylamino, alkenyloxyamino, alkinyloxy or        alkinylamino having in each case 2 to 6 carbon atoms,    -   represents in each case optionally cyano-, halogen- or        C₁-C₄-alkyl-substituted cycloalkyl, cycloalkyloxy,        cycloalkylamino, cycloalkylhydrazino, cycloalkylalkyl,        cycloalkylalkoxy or cycloalkylalkylamino having in each case 3        to 6 carbon atoms in the cycloalkyl group and, if appropriate, 1        to 4 carbon atoms in the alkyl moiety,    -   represents in each case optionally nitro-, cyano-, halogen-,        C₁-C₄-alkyl-, C₃-C₆-cycloalkyl-, C₁-C₄-halogenalkyl-,        C₁-C₄-alkoxy-, C₁-C₄-halogenalkoxy- or        C₁-C₄-alkoxy-carbonyl-substituted aryl, arylcarbonyl, aryloxy,        aryloxycarbonyl, arylthio, arylamino, arylhydrazino, arylalkyl,        arylalkoxy, arylalkylthio or arylalkylamino having in each case        6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to        4 carbon atoms in the alkyl moiety,    -   or represents in each case optionally nitro-, cyano-, halogen-,        C₁-C₄-alkyl-, C₃-C₆-cycloalkyl-, C₁-C₄-halogenalkyl-,        C₁-C₄-alkoxy-, C₁-C₄-halogenalkoxy-, C₁-C₄-alkylthio-,        C₁-C₄-halogenalkylthio- or C₁-C₄-alkoxy-carbonyl-substituted        monocyclic or bicyclic heterocyclyl, heterocyclyloxy,        heterocyclylthio, heterocyclylamino, the grouping        —N=(heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy,        heterocyclylalkylthio or heterocyclylalkylamino where in each        case the heterocyclyl grouping contains up to 10 carbon atoms        and additionally at least one heteroatom selected from the group        consisting of nitrogen (but at most 5 N atoms), oxygen (but at        most 2 O atoms), sulphur (but at most 2 S atoms), SO or SO₂ and,        if appropriate, additionally one group selected from the group        consisting of oxo (C═O), thioxo (C═S), imino (C═NH), cyanoimino        (C═N—CN), nitroimino (C═N—NO₂) and where, if appropriate, the        alkyl moiety contains 1 to 4 carbon atoms.-   R¹ particularly preferably represents in each case optionally    cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,    methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-,    ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl- or    ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-    or, t-butyl, represents in each case optionally cyano-, fluorine-,    chlorine- or bromine-substituted propenyl, butenyl, propinyl or    butinyl, or represents in each case optionally cyano-, fluorine-,    chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl,    cyclobutyl, cyclopentyl or cyclohexyl.-   R² particularly preferably represents hydrogen, cyano, carbamoyl,    thiocarbamoyl, fluorine, chlorine, bromine, represents in each case    optionally cyano-, fluorine-, chlorine-, methoxy- or    ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy,    n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or    i-propoxycarbonyl, represents in each case optionally fluorine-    and/or chlorine-substituted methylthio, ethylthio, n- or    i-propylthio, or represents in each case optionally cyano-,    fluorine-, chlorine-, bromine- methyl- or ethyl-substituted    cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.-   R³, R⁴ independently of one another particularly preferably    represent hydrogen, nitro, cyano, carboxyl, carbamoyl,    thiocarbamoyl, fluorine, chlorine, bromine, iodine, represent in    each case optionally fluorine-, chlorine-, methoxy-, ethoxy-,    methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-,    methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl n- or    i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,    n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio,    n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or    i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or    i-propylsulphonyl, represent methylamino, ethylamino, n- or    i-propylamino, n-, i-, s- or t-butylamino, dimethylamino,    diethylamino, dimethylaminocarbonyl, diethylaminocarbonyl,    dimethylaminosulphonyl or diethylaminosulphonyl.-   R⁵ particularly preferably represents hydrogen, represents in each    case optionally-cyano-, fluorine-, chlorine-, bromine-, methoxy-,    ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl,    n-, i-, s- or t-butyl, n-, i-, s-, or t-pentyl, methoxy, ethoxy, n-    or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or    i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,    ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,    ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-,    i-, s- or t-butylamino, represents dimethylamino or diethylamino,    represents in each case optionally fluorine-, chlorine- and/or    bromine-substituted ethenyl, propenyl, butenyl, pentenyl, ethinyl,    propinyl, butinyl or pentinyl, represents in each case optionally    cyano-, fluorine-, chlorine-, bromine-, methyl- orethyl-substituted    cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,    cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or    represents in each case optionally nitro-, cyano-, fluorine-,    chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl, n-, i-, s- or    t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,    difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylthio,    phenylsulphinyl, phenylsulphonyl, naphthyl, phenylnethyl,    phenylethyl, naphthylmethyl or naphthylethyl or represents the    grouping —C(Q)-Z.-   Y particularly preferably represents hydrogen, represents in each    case optionally cyano-, carbamoyl-, fluorine-, chlorine-, methoxy-,    ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or    i-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl,    represents in each case optionally fluorine- and/or    chlorine-substituted methylsulphonyl, ethylsulphonyl, n- or    i-propylsulphonyl, represents in each case optionally cyano-,    fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted    acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl,    ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl,    ethylaminocarbonyl, n- or i-propylaminocarbonyl, represents    dimethylaminocarbonyl or diethylaminocarbonyl, represents in each    case optionally cyano-, fluorine-, chlorine- or bromine-substituted    propenyl, butenyl, propenylcarbonyl, butenylcarbonyl, propinyl,    butinyl, propinylcarbonyl or butinylcarbonyl, represents in each    case optionally fluorine- and/or chlorine-substituted    propenylsulphonyl or butenylsulphonyl, represents in each case    optionally cyano-, fluorine-, chlorine-, methyl- or    ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,    cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl,    cyclohexylcarbonyl, cyclopropylmethyl, cyclobutylmethyl,    cyclopentylmethyl or cyclohexylmethyl, or represents in each case    optionally nitro-, cyano-, carbamoyl-, fluorine-, chlorine-,    bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,    trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,    difluoromethoxy- or trifluoromethoxy-substituted phenyl,    phenylsulphonyl, phenylcarbonyl, phenylmethyl, phenylethyl,    phenylmethylsulphonyl, phenylmethylcarbonyl or phenylcarbonylmethyl.-   Z particularly preferably represents amino, cyanoamino, nitroamino,    hydroxyamino, hydrazino,    -   represents in each case cyano-, methoxy-, ethoxy-, n- or        i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,        methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,        methylsulphonyl or ethylsulphonyl-substituted methyl, ethyl, n-        or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl,        methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,        methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or        t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-,        i-, s- or t-butylamino,    -   represents in each case optionally cyano-, fluorine-, chlorine-,        methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n-        or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or        i-propylsulphinyl-, methylsulphonyl- or        ethylsulphonyl-substituted methoxyamino, ethoxyamino, n- or        i-propoxyamino, n-, i-, s- or t-butoxyamino, methylhydrazino,        ethylhydrazino, n- or i-propylhydrazino, n-, i-, s- or        t-butylhydrazino, represents N-methylmethoxyamino or        dimethylhydrazino,    -   represents in each case optionally fluorine-, chlorine- and/or        bromine-substituted propenyloxy, butenyloxy, pentenyloxy,        propenylthio, butenylthio, pentenylthio, propenylamino,        butenylamino, pentenylamino, propenyloxyamino, butenyloxyamino,        pentenyloxyamino, propinyloxy, butinyloxy, pentinyloxy,        propinylamino, butinylamino or pentinylamino,    -   represents in each case optionally cyano-, fluorine-, chlorine-,        bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,        cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy,        cyclopentyloxy, cyclohexyloxy, cyclopropylamino,        cyclobutylamino, cyclopentylamino, cyclohexylamino,        cyclopropylhydrazino, cyclobutylhydrazino, cyclopentylhydrazino,        cyclohexylhydrazino, cyclopropylmethyl, cyclobutylmethyl,        cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy,        cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,        cyclopropylmethylamino, cyclobutylmethylamino,        cyclopentylmethylamino or cyclohexylmethylamino,    -   represents in each case optionally nitro-, cyano-, fluorine-,        chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-,        s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or        i-propoxy-, difluoromethoxy-, trifluoromethoxy-,        methoxycarbonyl-, ethoxycarbonyl-, n- or        i-propoxycarbonyl-substituted phenyl, phenylcarbonyl, phenoxy,        phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino,        naphthyl, naphthyloxy, naphthylthio, naphthylamino,        phenylmethyl, phenylethyl, phenylmethoxy, phenylethoxy,        phenylmethylthio, phenylethylthio, phenylmethylamino,        phenylethylamino, naphthylmethyl, naphthylethyl,        naphthylmethoxy, naphthylethoxy, naphthylmethylamino or        naphthylethylamino, or    -   represents in each case optionally nitro-, cyano-, fluorine-,        chlorine- bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s-        or t-butyl-, cyclopropyl-, cyclobutyl-, cyclopentyl-,        cyclohexyl-, difluoromethyl-, trifluormethyl-, dichloromethyl-,        trichloromethyl, chlorodifluoromethyl-, fluorodichloromethyl-,        methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-,        difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n-        or i-propylthio-, n-, i-, s- or t-butylthio-,        difluoromethylthio-, trifluoromethylthio, methoxycarbonyl-,        ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted monocyclic        or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylamino,        the grouping —N=(heterocyclyl), heterocyclylalkyl,        heterocyclylalkoxy or heterocyclylalkylamino from the group        consisting of furyl, furyloxy, furylamino, furylmethyl,        furylmethoxy, furylmethylamino, tetrahydrofuryl,        tetrahydrofuryloxy, tetrahydrofurylamino,        tetrathydrofurylmethyl, tetrahydrofurylmethoxy,        tetrahydrofurylmethylamino, dioxolanyl, dioxolanylmethyl,        dioxolanylmethoxy, dioxolanylmethylamino, thienyl, thienylamino,        thienylmethyl, thienylmethylamino, dithiolanyl,        dithiolanylmethyl, dithiolanylmethoxy, dithiolanylmethylamino,        pyrrolidinyl, pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl,        indolyl, pyrrolylmethyl, pyrazolyl, pyrazolyloxy,        pyrazolylamino, pyrazolylmethyl, imidazolyl, imidazolinyl,        imidazolylmethyl, iimidazolinylmethyl, oxoimidazolinyl,        2-oxo-1,3-diaza-cyclopentyl, oxazolyl, dihydrooxazolyl        (oxazolinyl), tetrahydrooxazolyl (oxazolidinyl), isoxazolyl,        dihydroisoxazolyl (isoxazolinyl), tetrahydroisoxazolyl        (isoxazolidinyl), tetrahydro-(2H)-1,2-oxazin-2-yl,        oxazolylmethyl, thiazolyl, dihydrothiazolyl (thiazolinyl),        tetrahydrothiazolyl (thiazolidinyl), thiazolimino,        thiazolylmethyl, dihydrothiazolyl (thiazolinyl),        tetrahydrothiazolyl (thiazolidinyl), oxothiazolidinyl,        cyanoiminothiazolidinyl, oxadiazolylamino, thiadiazolylamino,        oxotriazolinyl, oxotetrazolinyl, dioxanyl, dioxanylmethyl,        dioxanylmethoxy, dioxanylmethylamino, dithianyl,        dithianylmethyl, dithianylmethoxy, dithianylmethylamino,        triazolylamino, piperidinyl, piperidinylamino, oxopiperidinyl,        2-oxo-1,3-diaza-cyclohexyl, 2-oxo-1-aza-cycloheptyl,        2-oxo-1,3-diaza-cycloheptyl, morpholinyl, oxomorpholinyl,        morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy,        pyridinylamino, 2-(1H)-pyridinimino, pyridinylmethyl,        pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylmethyl        or pyrimidinylmethoxy.-   R¹ very particularly preferably represents methyl, ethyl, n- or    i-propyl, cyclopropyl, cyclopentyl or cyclohexyl.-   R² very particularly preferably represents hydrogen, represents in    each case optionally fluorine-, chlorine-, methoxy- or    ethoxy-substituted methyl, ethyl, methoxycarbonyl or ethoxycarbonyl,    represents in each case optionally fluorine- and/or    chlorine-substituted methylthio or ethylthio, or represents    optionally fluorine-, chlorine- or methyl-substituted cyclopropyl.-   R³, R⁴ independently of one another very particularly preferably    represent hydrogen, nitro, cyano, fluorine, chlorine, bromine,    methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl,    dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl,    methylsulphinylmethyl, methylsulphonylmethyl, methoxy, ethoxy,    difluoromethoxy, trifluoromethoxy, methylthio, ethylthio,    methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl or    dimethylaminosulphonyl.-   R⁵ very particularly preferably represents hydrogen, represents in    each case optionally cyano-, fluorine-, chlorine-, methoxy- or    ethoxy-substituted methyl, ethyl, n- or i-propyl, n- or i-butyl,    represents methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio,    n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or    i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino,    ethylamino, n- or i-propylamino or dimethylamino, represents in each    case optionally fluorine- and/or chlorine-substituted propenyl,    butenyl, propinyl or butinyl, represents in each case optionally    cyano-, fluorine-, chlorine- or methyl-substituted cyclopropyl,    cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,    cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or    represents in each case optionally nitro-, cyano-, fluorine-,    chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl, n-, i-, s- or    t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,    difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylthio,    phenylsulphinyl, phenylsulphonyl, phenylmethyl or phenylethyl, or    represents the grouping —C(Q)-Z.-   Y very particularly preferably represents hydrogen, represents in    each case optionally cyano-, fluorine-, methoxy-, ethoxy-,    methoxycarbonyl- or ethoxycarbonyl-substituted methyl or ethyl,    represents in each case optionally fluorine- and/or    chlorine-substituted methylsulphonyl or ethylsulphonyl, represents    in each case optionally cyano-, fluorine-, chlorine-, methoxy- or    ethoxy-substituted acetyl, propionyl, methoxycarbonyl,    ethoxycarbonyl, methylaminocarbonyl or ethylaminocarbonyl,    represents dimethylaminocarbonyl, represents in each case optionally    fluorine-, chlorine- or bromine-substituted propenyl,    propenylcarbonyl, propinyl or propinylcarbonyl, represents in each    case optionally cyano-, fluorine-, chlorine- or methyl-substituted    cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl,    cyclohexylcarbonyl, cyclopropylmethyl, cyclobutylmethyl,    cyclopentylmethyl or cyclohexylmethyl, or represents in each case    optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,    ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- or    trifluoromethoxy-substituted phenyl, phenylsulphonyl,    phenylcarbonyl, phenylmethyl, phenylmethylsulphonyl,    phenylmethylcarbonyl or phenylcarbonylmethyl.-   Z very particularly preferably represents amino, cyanoamino,    hydrazino,    -   represents in each case optionally cyano-, methoxy-, ethoxy-, n-        or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,        methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl-,        methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n-        or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or        i-propoxy, methylthio, ethylthio, n- or i-propylthio,        methylamino, ethylamino, n- or i-propylamino,    -   represents in each case optionally cyano-, fluorine-, chlorine-,        methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n-        or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or        i-propylsulphinyl-, methylsulphonyl- or        ethylsulphonyl-substituted methoxyamino, ethoxyamino, n- or        i-propoxyamino, methylhydrazino-, ethylhydrazino-, n- or        i-propylhydrazino, n-, i-, s- or t-butylhydrazino,        N-methyl-methoxyamino or dimethylhydrazino,    -   represents in each case optionally fluorine- and/or        chlorine-substituted propenyloxy, butenyloxy, propenylthio,        butenylthio, propenylamino, butenylamino, propenyloxyamino,        butenyloxyamino, propinyloxy, butinyloxy, propinylamino or        butinylamino,    -   represents in each case optionally cyano-, fluorine-, chlorine-        or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,        cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,        cyclohexyloxy, cyclopropylamino, cyclobutylamino,        cyclopentylamino, cyclohexylamino, cyclopentylhydrazino,        cyclohexylhydrazino, cyclopropylmethyl, cyclobutylmethyl,        cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy,        cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,        cyclopropylmethylamino, cyclobutylmethylamino,        cyclopentylmethylamino or cyclohexylmethylamino,    -   represents in each case optionally nitro-, cyano-, fluorine-,        chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-,        s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or        i-propoxy-, difluoromethoxy-, trifluoromethoxy-,        methoxycarbonyl-; ethoxycarbonyl-, n- or        i-propoxycarbonyl-substituted phenyl, phenylcarbonyl, phenoxy,        phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino,        phenylmethyl, phenylethyl, phenylmethoxy, phenylethoxy,        phenylmethylthio, phenylethylthio, phenylmethylamino or        phenylethylamino,    -   or represents in each case optionally nitro-, cyano-, fluorine-,        chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl, n-, i-, s-        or t-butyl-, cyclohexyl-, difluoromethyl-, trifluoromethyl-,        dichloromethyl-, trichloromethyl-, chlorodifluoromethyl-,        fluorodichloromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,        difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n-        or i-propylthio-, difluoromethylthio-, trifluoromethylthio-,        methoxycarbonyl-, ethoxycarbonyl-, n- or        i-propoxycarbonyl-substituted monocyclic or bicyclic        heterocyclyl, heterocyclyloxy, heterocyclylamino, the grouping        —N=(heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy or        heterocyclylalkylamino from the group consisting of furyl,        furyloxy, furylamino, furylmethyl, furylmethoxy,        furylmethylamino, tetrahydrofuryl, tetrahydrofuryloxy,        tetrahydrofurylamino, tetrahydrofurylmethyl,        tetrahydrofurylmethoxy, tetrahydrofurylmethylamino, dioxolanyl,        dioxolanylmethyl, dioxolanylmethoxy, dioxolanylmethylamino,        thienyl, thienylamino, thienylmethyl, thienylmethylamino,        dithiolanyl, dithiolanylmethyl, dithiolanylmethoxy,        dithiolanylmethylamino, pyrrolidinyl, pyrrolidinylamino,        oxopyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl, pyrazolyl,        pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl,        imidazolinyl, imidazolylmethyl, imidazolinylmethyl,        2-oxo-1,3-diaza-cyclopentyl, oxazolyl, oxazolylmethyl,        dihydrooxazolyl (oxazolinyl), tetrahydrooxazolyl (oxazolidinyl),        isoxazolyl, dihydroisoxazolyl (isoxazolinyl),        tetrahydroisoxazolyl (isoxazolidinyl),        tetra-hydro-(2H)-1,2-oxazin-2-yl, thiazolyl, thiazolylmethyl,        dihydrothiazolyl (thiazolinyl), tetrahydrothiazolyl        (thiazolidinyl), thiazolimino, oxothiazolidinyl,        cyanoiminothiazolidinyl, oxadiazolylamino, thiadiazolylamino,        oxotriazolinyl, oxotetrazolinyl, dioxanyl, dioxanylmethyl,        dioxanylmethoxy, dioxanylmethylamino, dithianyl,        dithianylmethyl, dithianylmethoxy, dithianylmethylamino,        triazolylamino, piperidinyl, piperidinylamino, oxopiperidinyl,        2-oxo-1,3-diaza-cyclohexyl, 2-oxo-1-aza-cycloheptyl,        2-oxo-1,3-diaza-cycloheptyl, morpholinyl, oxo-morpholinyl,        morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy,        pyridinylamino, 2-(1H)-pyridinimino, pyridinylmethyl,        pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylmethyl        or pyrimidinylmethoxy.

A very particularly preferred group are those compounds of the generalformula (I) in which

-   Q represents O or S,-   R¹ represents methyl, ethyl, n- or i-propyl,-   R² represents hydrogen, methyl, ethyl, methoxycarbonyl,    ethoxycarbonyl, methylthio or ethylthio,-   R³, R⁴ independently of one another represent hydrogen, nitro,    cyano, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,    trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl,    methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl,    methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio,    ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl,    ethylsulphonyl or dimethylaminosulphonyl,-   R⁵ represents hydrogen, represents methyl, ethyl, n- or i-propyl,    represents methylthio, ethylthio, n- or i-propylthio,    methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,    methylsulphonyl or ethylsulphonyl, represents in each case    optionally fluorine- and/or chlorine-substituted propenyl, butenyl,    propinyl or butinyl, or represents cyclopropyl,-   Y represents hydrogen, represents in each case optionally cyano-,    fluorine-, methoxy-, ethoxy-, methoxycarbonyl- or    ethoxycarbonyl-substituted methyl or ethyl, represents in each case    optionally fluorine- and/or chlorine-substituted methylsulphonyl or    ethylsulphonyl, represents in each case optionally cyano-,    fluorine-, chlorine-, methoxy- or ethoxy-substituted acetyl,    propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl or    ethylaminocarbonyl, represents dimethylaminocarbonyl, represents in    each case optionally fluorine-, chlorine- or bromine-substituted    propenyl, propenylcarbonyl, propinyl or propinylcarbonyl, represents    in each case optionally cyano-, fluorine-, chlorine- or    methyl-substituted cyclopropylcarbonyl, cyclobutylcarbonyl,    cyclopentylcarbonyl, cyclohexylcarbonyl, cyclopropylmethyl,    cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or    represents in each case optionally nitro-, cyano-, fluorine-,    chlorine-, bromine-, methyl-, ethyl-, trifluoromethyl-, methoxy-,    ethoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl,    phenylsulphonyl, phenylcarbonyl, phenylmethyl,    phenylmethylsulphonyl, phenylmethylcarbonyl or phenylcarbonylmethyl    and-   Z represents amino, cyanoamino, hydrazino, represents methoxyamino,    ethoxyamino, n- or i-propoxyamino, methylhydrazino, ethylhydrazino,    n- or i-propylhydrazino, n-, i-, s- or t-butylhydrazino, represents    N-methylmethoxyamino or dimethylhydrazino, represents in each case    optionally fluorine- and/or chlorine-substituted propenyloxy,    butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino,    propenyloxyamino, butenyloxyamino, propinyloxy, butinyloxy,    propinylamino or butinylamino,    -   represents in each case optionally cyano-, fluorine-, chlorine-        or methyl-substituted cyclopropyl, cyclopentyl, cyclohexyl,        cyclopropyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino,        cyclopentylamino, cyclohexylamino, cyclohexylhydrazino,        cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl,        cyclopropylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,        cyclopropylmethylamino, cyclopentylmethylamino or        cyclohexylmethylamino,    -   represents in each case optionally nitro-, cyano-, fluorine-,        chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-,        s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or        i-propoxy-, difluoromethoxy-, trifluoromethoxy-,        methoxycarbonyl-, ethoxycarbonyl-, n- or        i-propoxycarbonyl-substituted phenyl, phenylcarbonyl, phenoxy,        phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino,        phenylmethyl, phenylethyl, phenylmethoxy, phenylethoxy,        phenylmethylthio, phenylethylthio, phenylmethylamino or        phenylethylamino, or    -   represents in each case optionally nitro-, cyano-, fluorine-,        chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-,        s- or t-butyl-, cyclopropyl-, cyclobutyl-, cyclopentyl-,        cyclohexyl-, difluoromethyl-, trifluoromethyl-, dichloromethyl-,        trichloromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-,        methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-,        trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-,        difluoromethylthio-, trifluoromethylthio-, methoxycarbonyl-,        ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted monocyclic        or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylamino,        heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkylamino        from the group consisting of furyl, fuloxy, furylamino,        furylmethyl, furylmethoxy, furylmethylamino, tetrahydrofuryl,        tetrahydrofuryloxy, tetrahydrofurylamino, tetrahydrofurylmethyl,        tetrahydrofurylmethoxy, tetrahydrofurylmethylamino, dioxolanyl,        dioxolanylmethyl, dioxolanylmethoxy, dioxolanylmethylamino,        thienyl, thienylamino, thienylmethyl, thienylmethylamino,        dithiolanyl, dithiolanylmethyl, dithiolanylmethoxy,        dithiolanylmethylamino, pyrrolidinyl, pyrrolidinylamino,        oxo-pyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl, pyrazolyl,        pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl,        imidazolinyl, imidazolylmethyl, imidazolinylmethyl,        2-oxo-1,3-diaza-cyclopentyl, oxazolyl, oxazolylmethyl,        dihydrooxazolyl (oxazolinyl), tetrahydrooxazolyl (oxazolidinyl),        isoxazolyl, dihydroisoxazolyl (isoxazolinyl),        tetrahydroisoxazolyl (isoxazolidinyl), thiazolyl,        thiazolylmethyl, dihydrothiazolyl (thiazolinyl),        tetrahydrothiazolyl (thiazolidinyl), oxothiazolidinyl,        cyanoiminothiazolidinyl, oxotriazolinyl, oxotetrazolinyl,        dioxanyl, dioxanylmethyl, dioxanylmethoxy, dioxanylmethylamino,        dithianyl, dithianylmethyl, dithianylmethoxy,        dithianylmethylamino, triazolylamino, piperidinyl,        piperidinylamino, oxopiperidinyl, 2-oxo-1,3-diaza-cyclohexyl,        2-oxo-1-aza-cycloheptyl, 2-oxo-1,3-diaza-cycloheptyl,        morpholinyl, oxomorpholinyl, morpholinylamino, piperazinyl,        pyridinyl, pyridinyloxy, pyridinylamino, pyridinylmethyl,        pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy,        pyrimidinylmethyl, pyrimidinylmethoxy.

Particular emphasis is given to the compounds of the formulae (I-1) to(I-3):

Here, Q, R¹, R², R³, R⁴, R⁵, Y and Z in each case have the meaningsgiven above as being preferred, particularly preferred or veryparticularly preferred.

Particular emphasis is also given to the compounds of the formulae(I-a), (I-b) and (I-c):

Here, Q, Z, R¹, R², R³, R⁴ and R⁵ in each case have the meanings givenabove as being preferred, particularly preferred or very particularlypreferred.

The general or preferred radical definitions given above apply both tothe end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation.

The radical definitions can be combined with one another as desired,i.e. including combinations between the given preferred ranges.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred.

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Unless defined otherwise, the following definitions apply in thedefinitions given above and below:

Saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl,alkenyl or alkinyl, are in each case straight-chain or branched,including in combination with heteroatoms, such as, for example, inalkoxy, alkylthio or alkylamino. Unless indicated otherwise, preferenceis given to hydrocarbon chains having 1 to 6 carbon atoms.

Aryl represents aromatic mono- or polycyclic hydrocarbon rings, such as,for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenylor naphthyl, in particular phenyl.

Heterocyclyl represents saturated, unsaturated or aromatic cycliccompounds in which at least one ring atom is a heteroatom, i.e. an atomdifferent from carbon. If the ring contains a plurality of heteroatoms,these can be identical or different. Preferred heteroatoms are oxygen,nitrogen and sulphur. If the ring contains a plurality of oxygen atoms,these are not adjacent. If appropriate, the cyclic compounds may form apolycyclic ring system together with further carbocyclic or heterocyclicfused-on or bridged rings. A polycyclic ring system can be attached viathe heterocyclic ring or a fused-on carbocyclic ring. Preference isgiven to mono- or bicyclic ring systems, in particular to monocyclicring systems having 5 or 6 ring members and to bicyclic ring systemshaving 7 to 9 ring members.

Cycloalkyl represents saturated, carbocyclic compounds which, ifappropriate, form a polycyclic ring system together with furthercarbocyclic fused-on or bridged rings.

Unless indicated otherwise, preference is given to cyclopropyl,cyclopentyl and cyclohexyl.

The novel substituted benzoylpyrazoles of the general formula (I) havestrong and selective herbicidal activity.

The novel substituted benzoylpyrazoles of the general formula (I)obtained when

-   a) pyrazoles of the general formula (II)

in which

-   R¹, R² and Y are as defined above-   are reacted with substituted benzoic acids of the general formula    (III)

in which

-   Q, R³, R⁴, R⁵ and Z are as defined above    -   or with reactive derivatives thereof, such as, for example, the        corresponding acid halides, acid anhydrides, acid cyanides or        esters,-   if appropriate in the presence of a dehydrating agent, if    appropriate in the presence of one or more reaction auxiliaries and    if appropriate in the presence of one or more diluents,    or when-   (b) substituted benzoylpyrazoles of the general formula (Ia)

in which

-   Q, R¹, R², R³, R⁴, R⁵ and Z are as defined above,-   are reacted with compounds of the general formula (IV)    X—Y  (IV)    in which-   Y is as defined above, except for hydrogen, and-   X represents halogen,    -   or, if appropriate, with corresponding acid anhydrides,        isocyanates or isothiocyanates-   if appropriate in the presence of one or more reaction auxiliaries    and if appropriate in the presence of one or more diluents,-   and, if appropriate, the resulting compounds of the formula (I) are    subsequently subjected, in a customary manner, to electrophilic or    nucleophilic substitution reactions and/or oxidation or reduction    reactions, or the compounds of the formula (I) are, in a customary    manner, converted into salts.

In principle, the novel substituted benzoylpyrazoles of the generalformula (I) can also be obtained as shown schematically below:

-   (c) by reacting aminobenzoylpyrazoles of the general formula (V)    with halogeno-(thio)carbonyl compounds of the general formula (VI)    or, if appropriate, with corresponding iso(thio)cyanates (here, Q,    R¹, R², R³, R⁴, R⁵, Y and Z are as defined above, X represents    halogen):

-   (d) by reacting iso(thio)cyanatobenzoylpyrazoles of the general    formula (VII) with nucleophilic compounds of the general    formula (VIII) (here, Q, R¹, R², R³, R⁴, Y and Z are as defined    above):

-   Using, for example, 3-chloro-5-hydroxy-1-methyl-pyrazol and    3-[(cyclopropylaminocarbonyl)-(methylamino)]-5-fluoro-benzoic acid    as starting materials, the course of the reaction in the process (a)    according to the invention can be illustrated by the formula scheme    below:

-   Using, for example, 2-methoxy-ethyl    N-[3-chloro-4-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-phenyl]-N-ethyl-carbamate    and benzoyl chloride as starting materials, the course of the    reaction in the process (b) according to the invention can be    illustrated by the formula scheme below:

The formula (II) provides a general definition of the pyrazoles to beused as starting materials in the process (a) according to the inventionfor preparing compounds of the general formula (I). In the generalformula (II), R¹, R² and Y preferably have those meanings which havealready been mentioned above, in connection with the description of thecompounds of the general formula (I) according to the invention, asbeing preferred, particularly preferred or very particularly preferredfor R¹, R² and Y.

The starting materials of the general formula (II) are known and/or canbe prepared by processes known per se (cf. EP-A-240 001).

The formula (III) provides a general definition of the substitutedbenzoic acids further to be used as starting materials in the process(a) according to the invention. In the formula (III) Q, R³, R⁴, R⁵ and Zpreferably have those meanings which have already been mentioned above,in connection with the description of the compounds of the formula (I)according to the invention, as being preferred, particularly preferredor very particularly preferred for Q, R³, R⁴, R⁵ and Z.

The starting materials of the general formula (III) are known and/or canbe prepared by processes per se (cf. JP-A-112 92 849 and PreparationExamples).

The substituted benzoic acids of the general formula (III) are obtainedwhen benzoic acid esters of the general formula (IIIa)

in which

-   Q, R³, R⁴, R⁵ and Z are as defined above and-   R represents alkyl, in particular methyl or ethyl,-   are reacted with water, if appropriate in the presence of a    hydrolysis auxiliary, such as, for example, aqueous sodium hydroxide    solution, and if appropriate in the presence of a diluent, such as,    for example, tetrahydrofuran, at temperatures between 0° C. and    100° C. (cf. the Preparation Examples).

The benzoic acid esters of the general formula (IIIa) required asprecursors are known and/or can be prepared by processes known per se(cf. JP-A-112 92 849 and Preparation Examples).

The benzoic acid esters of the general formula (IIIa) are obtained when

-   (α) aminobenzoic acid esters of the general formula (IX)

in which

-   Q, R³, R⁴, R⁵ and Z are as defined above and-   R represents alkyl, in particular methyl or ethyl,-   are reacted with halogeno(thio)carbonyl compounds of the general    formula (VI)

in which

-   Q and Z are as defined above and-   X represents halogen, in particular fluorine, chlorine or bromine,    -   or, if appropriate, with the corresponding iso(thio)cyanates-   if appropriate in the presence of an acid acceptor, such as, for    example, potassium carbonate or triethylamine, and if appropriate in    the presence of a diluent, such as, for example, methyl isobutyl    ketone or acetonitrile, at temperatures between 0° C. and 100° C.    (cf. the Preparation Examples),    or when-   (β) iso(thio)cyanatobenzoic acid esters of the general formula (X)

in which

-   Q, R³ and R⁴ are as defined above and-   R represents alkyl, in particular methyl or ethyl,-   are reacted with nucleophilic compounds of the general formula    (VIII)

in which

-   Z is as defined above,-   if appropriate in the presence of a reaction auxiliary, such as, for    example, triethylamine, and if appropriate in the presence of a    diluent, such as, for example, acetonitrile or toluene, at    temperatures between 10° C. and 120° C. (cf. the Preparation    Examples).

The formula (Ia) provides a general definition of the substitutedbenzoylpyrazoles to be used as starting materials in the process (b)according to the invention for preparing compounds of the generalformula (I). In the general formula (Ia), Q, R¹, R², R³, R⁴, R⁵ and Zpreferably have those meanings which have already been mentioned above,in connection with the description of the compounds of the generalformula (I) according to the invention, as being preferred, particularlypreferred or very particularly preferred for Q, R¹, R², R³, R⁴, R⁵ andZ.

The starting materials of the general formula (Ia) are novel compoundsaccording to the invention; they can be prepared by process (a)according to the invention.

The formula (IV) provides a general definition of the compounds furtherto be used as starting materials in the process (b) according to theinvention. In the general formula (IV), Y preferably has that meaningwhich has already been mentioned above, in connection with thedescription of the compounds of the general formula (I) according to theinvention, as being preferred, particularly preferred or veryparticularly preferred for Y; X preferably represents fluorine,chlorine, bromine or iodine, in particular chlorine or bromine.

The starting materials of the general formula (IV) are known chemicalsfor synthesis.

The formulae (V) and (VI) provide general definitions of the compoundsfurther to be used as starting materials in the process (c) according tothe invention for preparing compounds of the general formula (I). In thegeneral formulae (V) and (VI), Q, R¹, R², R³, R⁴, R⁵, X and Z preferablyhave that meaning which has already been mentioned above, in connectionwith the description of the general formula (I), as being preferred,particularly preferred or very particularly preferred for Q, R¹, R², R³,R⁴, R⁵, X and Z. The starting materials of the general formula (VI) areknown organic compounds. The starting materials of the general formula(V) can be prepared by processes known per se.

The formulae (VII) and (VIII) provide general definitions of thecompounds to be used as starting materials in the process (d) accordingto the invention for preparing compounds of the general formula (I). Inthe general formulae (VII) and (VIII), Q, R¹, R², R³, R⁴, R⁵, Y and Zpreferably have that meaning which has already been mentioned above, inconnection with the description of the general formula (I), as beingpreferred, particularly preferred or very particularly preferred.

The starting materials of the general formula (VIII) are known chemicalsfor synthesis. The starting materials of the general formula (VII) canbe prepared by processes known per se.

The formula (IX) provides a general definition of the compounds to beused as starting materials in the process (α) according to the inventionfor preparing compounds of the general formula (IIIa). In the generalformula (IX), R³, R⁴ or R⁵ preferably have that meaning which hasalready been mentioned above, in connection with the description of thegeneral formula (I), as being preferred, particularly preferred or veryparticularly preferred.

The formula (X) provides a general definition of the compounds to beused as starting materials in the process (β) according to the inventionfor preparing compounds of the formula (IIIa). In the general formula(X), Q, R³ and R⁴ preferably have that meaning which has already beenmentioned above, in connection with the description of the generalformula (I), as being preferred, particularly preferred or veryparticularly preferred.

The starting materials of the general formula (X) can be prepared byprocesses know per se.

The process (a) according to the invention for preparing novelsubstituted benzoylpyrazoles of the general formula (I) is preferablycarried out using a dehydrating agent. Suitable dehydrating agents arethe customary chemicals suitable for binding water.

Examples which may be mentioned are dicyclohexylcarbodiimide,propanephosphonic anhydride and carbonyl-bis-imidazole.

Dehydrating agents which may be mentioned as being particularly suitableare dicyclohexylcarbodiimide and propanephosphonic anhydride.

The process (a) according to the invention for preparing the novelsubstituted benzoylpyrazoles of the general formula (I) is, ifappropriate, carried out using a reaction auxiliary.

Examples of suitable reaction auxiliaries which may be mentioned aresodium cyanide, potassium cyanide, acetone cyanohydrin,2-cyano-2-(trimethylsilyloxy)-propane and trimethylsilyl cyanide.

A reaction auxiliary which may be mentioned as being particularlysuitable is trimethylsilyl cyanide.

The processes (a) and (b) according to the invention are preferablycarried out using one or more reaction auxiliaries. Suitable reactionauxiliaries for the processes (a) and (b) according to the inventionare, in general, the customary inorganic or organic bases or acidacceptors. These preferably include alkali metal or alkaline earth metalacetates, amides, carbonates, bicarbonates, hydrides, hydroxides oralkoxides, such as, for example, sodium acetate, potassium acetate orcalcium acetate, lithium amide, sodium amide, potassium amide or calciumamide, sodium carbonate, potassium carbonate or calcium carbonate,sodium bicarbonate, potassium bicarbonate or calcium bicarbonate,lithium hydride, sodium hydride, potassium hydride or calcium hydride,lithium hydroxide, sodium hydroxide, potassium hydroxide or calciumhydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- ort-butoxide; furthermore also basic organic nitrogen compounds, such as,for example, trimethylamine, triethylamine, tripropylamine,tributylamine, ethyl-diisopropylamine, N,N-dimethylcyclohexylamine,dicyclohexylamine, ethyl-dicyclohexylamine, N,N-dimethyl-aniline,N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-,2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine,5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine,N-methyl-piperidine, N-ethylpiperidine, N-methyl-morpholine,N-ethyl-morpholine, 1,4-diazabicyclo[2.2.2]-octane (DABCO),1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or1,8-diazabicyclo[5.4.0]-undec-7-ene(DBU).

Further reaction auxiliaries suitable for the processes (a) and (b)according to the invention are phase-transfer catalysts. Examples ofsuch catalysts which may be mentioned are:

Tetrabutylammonium bromide, tetrabutylammonium chloride,tetraoctylammonium chloride, tetrabutylammonium hydrogen sulphate,methyl-trioctylammonium chloride, hexadecyl-trimethylammonium chloride,hexadecyl-trimethylammonium bromide, benzyl-trimethylammonium chloride,benzyl-triethylammonium chloride, benzyl-trimethylammonium hydroxide,benzyl-triethylammonium hydroxide, benzyltributylammonium chloride,benzyl-tributylammonium bromide, tetrabutylphosphonium bromide,tetrabutylphosphonium chloride, tributyl-hexadecylphosphonium bromide,butyl-triphenylphosphonium chloride, ethyl-trioctylphosphonium bromide,tetraphenylphosphonium bromide.

The processes according to the invention for preparing the compounds ofthe general formula (I) are in each case preferably carried out usingone or more diluents. Suitable diluents for carrying out the processes(a) and (b) according to the invention are, in addition to water,especially inert organic solvents. These include, in particular,aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons,such as, for example, benzine, benzene, toluene, xylene, chlorobenzene,dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane,chloroform, carbon tetrachloride; ethers, such as diethyl ether,diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethylether or ethylene glycol diethyl ether; ketones, such as acetone,butanone or methyl isobutyl ketone; nitriles, such as acetonitrilepropionitrile or butyronitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone orhexamethyl-phosphoric triamide; esters, such as methyl acetate or ethylacetate, sulphoxides, such as dimethyl sulphoxide, alcohols, such asmethanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether,ethylene glycol monoethyl ether, diethyelene glycol monomethyl ether,diethylene glycol monoethyl ether, mixtures thereof with water or purewater.

When carrying out the processes (a) and (b) according to the invention,the reaction temperatures can be varied within a relatively wide range.In general, the processes are carried out at temperatures between 0° C.and 150° C., preferably between 10° C. and 120° C.

The processes according to the invention are generally carried out underatmospheric pressure. However, it is also possible to carry out theprocesses according to the invention under elevated or reducedpressure—in general between 0.1 bar and 10 bar.

For carrying out the processes according to the invention, the startingmaterials are generally employed in approximately equimolar amounts.However, it is also possible to use a relatively large excess of one ofthe components. The reaction is generally carried out in a suitablediluent in the presence of a reaction auxiliary, and the reactionmixture is generally stirred at the required temperature for a number ofhours. Work-up is carried out by customary methods (cf. the PreparationExamples).

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.Weeds in the broadest sense are understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lam ium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbaria, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The active compounds according to the invention are suitable, dependingon the concentration, for the total control of weeds, for example onindustrial terrain and rail tracks, and on paths and areas with andwithout tree plantings. Similarly, the active compounds according to theinvention can be employed for controlling weeds in perennial crops, forexample forests, decorative tree plantings, orchards, vineyards, citrusgroves, nut orchards, banana plantations, coffee plantations, teaplantations, rubber plantations, oil palm plantations, cocoaplantations, soft fruit plantings and hop fields, on lawns, turf andpastureland, and for the selective control of weeds in annual crops.

The compounds of the formula (I) according to the invention have strongherbicidal. activity and a broad active spectrum when used on the soiland on above-ground parts of plants. To a certain extent they are alsosuitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and di-cotyledonous crops, bothby the pre-emergence and by the post-emergence method.

At certain concentrations or application rates, the active compoundsaccording to the invention can also be employed for controlling animalpests and fungal or bacterial plant diseases. If appropriate, they canalso be used as intermediates or precursors for the synthesis of otheractive compounds.

According to the invention, it is possible to treat all plants and partsof plants. Plants are to be understood here as meaning all plants andplant populations such as desired and undesired wild plants or cropplants (including naturally occurring crop plants). Crop plants can beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding plant cultivars which can or cannot be protected by plantbreeders certificates. Parts of plants are to be understood as meaningall above-ground and below-ground parts and organs of plants, such asshoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stems, tniks, flowers, fruit-bodies, fruits and seedsand also roots, tubers and rhizomes. Parts of plants also includeharvested plants and vegetative and generative propagation material, forexample seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormulti-layer coating.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspo-emulsion concentrates,natural and synthetic substances impregnated with active compound, andmicroencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is to say liquid solventsand/or solid carriers, optionally with the use of surfactants, that isto say emulsifiers and/or dispersants and/or foam-formers.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Liquid solvents which are mainlysuitable are: aromatics, such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols, such as butanol orglycol, and also their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents, such as dimethylformamide and dimethyl sulphoxide, andwater.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks, such as calcite, marble, pumice, sepiolite, dolomite andsynthetic granules of inorganic and organic meals, and granules oforganic material, such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers, such as carboxylmethylcellulose, natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants, such as inorganic pigments, for exampleiron oxide, titanium oxide, Prussian blue, and organic dyestuffs, suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients, such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in their formulations, can also be used as mixtures withknown herbicides and/or substances which improve the compatibility withcrop plants (“safeners”), finished formulations or tank mixes beingpossible. Also possible are mixtures with weed-killers comprising one ormore known herbicides and a safener.

Possible components for the mixtures are known herbicides, for example

-   acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim    (-sodium), ametryne, amicarbazone, amidochlor, amidosulphuron,    anilofos, asulam, atrazine, azafenidin, azimsulphuron,    beflubutarnid, benazolin (-ethyl), benfuresate, bensulphuron    (-methyl), bentazon, benzfendizone, benzobicyclon, benzofenap,    benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium),    bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil    (-allyl), butroxydim, butylate, cafenstrole, caloxydim, carbetamide,    carfentrazone (-ethyl), chlomethoxyfen, chloramben, chloridazon,    chlorimuron (-ethyl), chl oritrofen, chlorsulphuron, chlortoluron,    cinidon (-ethyl), cinmethylin, cinosulphuron, clefoxydim, clethodim,    clodinafop (-propargyl), clomazone, clomeprop, clopyralid,    clopyrasulphuron (-methyl), cloransulam (-methyl), cumyluron,    cyanazine, cybutryne, cycloate, cyclosulphamuron, cycloxydim,    cyhalofop (-butyl), 2,4-D, 2,4-DB, desmedipham, diallate, dicamba,    dichlorprop (-P), diclofop (-methyl), diclosulam, diethatyl    (-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron,    dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam,    dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron,    epropodan, EPTC, esprocarb, ethalfluralin, ethametsulphuron    (-methyl), ethofumesate, ethoxyfen, ethoxysulphuron, etobenzanid,    fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl,    -isopropyl-L, -methyl), flazasulphuron, florasulam, fluazifop    (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet,    flumetsulaam, flumiclorac (-pentyl), flumioxazin, flumipropyn,    flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl),    flupoxam, flupropacil, flurpyrsulphuron (-methyl, -sodium), flurenol    (-butyl), fluridone, fluroxypyr (-butoxypropyl, -meptyl),    flurprimidol, flurtamone, fluthiacet (-methyl), fluthiamide,    fomesafen, foramsulphuron, glufosinate (-ammonium), glyphosate    (-isopropylammonium), halosafen, haloxyfop (-ethoxy-ethyl,    -P-methyl), hexazinone, imazamethabenz (-methyl), imazamethapyr,    imazamox, imazapic, imazapyr, imazaquin, imazethapyr,    imazosulphuron, iodosulphuron (-methyl, -sodium), ioxynil,    isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,    isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA,    mecoprop, mefenacet, mesosulphuron, mesotrione, metamitron,    metazachlor, methabenzthiazuron, metobenzuron, metobromuron,    (alpha-) metolachlor, metosulam, metoxuron, metribuzin, metsulphuron    (-methyl), molinate, monolinuron, naproanilide, napropamide,    neburon, nicosulphuron, norflurazon, orbencarb, oryzalin,    oxadiargyl, oxadiazon, oxasulphuron, oxaziclomefone, oxyfluorfen,    paraquat, pelargon acid, pendimetha in, pendralin, pentoxazone,    phenmedipham, picolinafen, piperophos, pretilachlor, primisulphuron    (-methyl), profluazol, prometryn, propachlor, propanil,    propaquizafop, propisochlor, procarbazone (-sodium), propyzamide,    prosulphocarb, prosulphuron, pyraflufen (-ethyl), pyrazogyl,    pyrazolate, pyrazosulphuron (-ethyl), pyrazoxyfen, pyribenzoxim,    pyributicarb, pyridate, pyridatol, pyriftalid, pyriminobac    (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac,    quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulphuron,    sethoxydim, simazine, simetryn, sulcotrione, sulphentrazone,    sulphometuron (-methyl), sulphosate, sulphosulphuron, tebutam,    tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor,    thiafluamide, thiazopyr, thidiazimin, thifensulphuron (-methyl),    thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulphuron,    tribenuron (-methyl), triclopyr, tridiphane, trifluralin,    trifloxysulphuron, triflusulphuron (-methyl), tritosulphuron.

Furthermore suitable for the mixtures are known softeners, for example

-   AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl), cyometrinil,    2,4-D, DKA-24, dichlormid, dymron, fenclorim, fenchlorazol (-ethyl),    flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), MCPA,    mecoprop (-P), mefenpyr (-diethyl), MG-191, oxabetrinil, PPG-1292,    R-29148.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in a customary manner, for example bywatering, spraying, atomizing or broadcasting.

The active compounds according to the invention can be applied bothbefore and after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding, such as crossing or protoplast fusion, and partsthereof, are treated. In a further preferred embodiment, transgenicplants and plant cultivars obtained by genetic engineering, ifappropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingcertain properties (“traits”) and which have been obtained byconventional breeding, by mutagenesis or by recombinant DNA techniques.They can be cultivars, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions to be used according to theinvention—also in combination with other agro-chemical activecompounds—, better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products are possible whichexceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by geneticengineering) which are preferably treated according to the inventioninclude all plants which, in the genetic modification, received geneticmaterial which imparted particularly advantageous useful properties(“traits”) to these plants. Examples of such properties are better plantgrowth, increased tolerance to high or low temperatures, increasedtolerance to drought or to water or soil salt content, increasedflowering performance, easier harvesting, accelerated maturation, higherharvest yields, better quality and/or a higher nutritional value of theharvested products, better storage stability and/or processability ofthe harvested products. Further and particularly emphasized examples ofsuch properties are a better defence of the plants against animal andmicrobial pests, such as against insects, mites, phytopathogenic fungi,bacteria and/or viruses, and also increased tolerance of the. plants tocertain herbicidally active compounds. Examples of transgenic plantswhich may be mentioned are the important crop plants, such as cereals(wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape andalso fruit plants (with the fruits apples, pears, citrus fruits andgrapes), and particular emphasis is given to maize, soya beans,potatoes, cotton and oilseed rape. Traits that are emphasized are inparticular increased defence of the plants against insects by toxinsformed in the plants, in particular those formed in the plants by thegenetic material from Bacillus thuringiensis (for example by the genesCryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab,Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred toas “Bt plants”). Traits that are also particularly emphasized are theincreased defence of the plants to fungi, bacteria and viruses bysystemic acquired resistance (SAR), systemin, phytoalexins, elicitorsand resistance genes and correspondingly expressed proteins and toxins.Traits that are furthermore particularly emphasized are the increasedtolerance of the plants to certain herbicidally active compounds, forexample imidazolinones, sulphonylureas, glyphosate or phosphinotricin(for example the “PAT” gene). The genes which impart the desired traitsin question can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for examplemaize, cotton, soya beans), KnockOut® (for example maize), StarLink®(for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya bean), Liberty Link® (tolerance tophosphinotricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulphonylurea, for examplemaize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned include the varietiessold under the name Clearfield® (for example maize). Of course, thesestatements also apply to plant cultivars having these genetic traits orgenetic traits still to be developed, which plants will be developedand/or marketed in the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula (I) or the active compound mixtures according to the invention,where in addition to the good control of weed plants, the abovementionedsynergistic effects with the transgenic plants or plant cultivars occur.The preferred ranges stated above for the active compounds or mixturesalso apply to the treatment of these plants. Particular emphasis isgiven to the treatment of plants with the compounds or mixturesspecifically mentioned in the present text.

The following examples show the preparation and use of the activecompounds according to the invention:

PREPARATION EXAMPLES Example 1

(Process (a))

A mixture of 2.80 g (8.43 mMol) of2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl)-carbonyl]-amino]-benzoicacid, 0.945 g (8.43 mMol) of 1-ethyl-5-hydroxy-pyrazole, 2.10 g (10.1mmol) of dicyclohexylcarbodiimide and 30 ml of acetonitrile is stirredat room temperature (about 20° C.) for 18 hours and then filtered. 0.335g (3.37 mMol) of trimethylsilyl cyanide and 1.70 g (16.9 mMol) oftriethylamine are added to the filtrate and the mixture is stirred atroom temperature for 18 hours and then concentrated under reducedpressure. The residue is stirred with 10% strength aqueous sodiumcarbonate solution and then shaken with diethyl ether. The organic phaseis separated off (and discarded) and the aqueous solution is thenacidified with conc. hydrochloric acid, and the resulting crystallineproduct is isolated by filtration with suction.

This gives 1.60 g (32.5% of theory) ofN-[2,6-dichloro-3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-phenyl]-3-methyl-2-oxo-1-imidazolidinecarboxamide.

logP (pH=2.3): 1.58.

Analogously to Example 1, and in accordance with the general descriptionof the preparation process according to the invention, it is alsopossible to prepare, for example, the compounds of the general formula(I)—or of the formulae (I-1), (I-2) or (I-3)—listed in Table I below.

TABLE 1 (I-1)

(I-2)

(I-3)

Examples of the compounds of the formulae (I), (I-1), (I-2), (I-3) Here,Y in each case represents hydrogen Ex.- (position) (position) FormulaNo. Q R¹ R² R³ R⁴ R⁵ Z Physical Data 2 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1,39^(a)) 3 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.13^(a)) 4 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.32^(a)) 5 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.83^(a)) 6 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.13^(a)) 7 O C₂H₅ H (4) CF₃ — H

(I-1) logP = 2.93^(a)) 8 O CH₃ H (4) CF₃ — H

(I-1) logP = 2.50^(a)) 9 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.55^(a)) 10 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 0.82^(a)) 11 O C₂H₅ H (4) CF₃ — H

(I-1) logP = 2.42^(a)) 12 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.63^(a)) 13 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.86^(a)) 14 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.25^(a)) 15 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.03^(a)) 16 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.17^(a)) 17 O CH₃ H (4) CF₃ — H

(I-1) logP = 2.12^(a)) 18 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 2.11^(a)) 19 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.83^(a)) 20 O CH₃ H (2) Cl (4) Cl H

(I-2) 21 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 0.99^(a)) 22 O CH₃ H (2) Cl (4) Cl H

(I-2) 23 O CH₃ H (2) Cl (4) Cl H

(I-2) 24 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.18^(a)) 25 O CH₃ H (2) Cl (4) Cl H

(I-2) 26 O CH₃ H (2) Cl (4) Cl H

(I-2) 27 O CH₃ H (2) Cl (4) Cl H

(I-2) 28 O CH₃ H (2) Cl (4) Cl H

(I-2) 29 O CH₃ H (2) Cl (4) Cl H

(I-2) 30 O CH₃ H (2) Cl (4) Cl H

(I-2) 31 O CH₃ H (2) Cl (4) Cl H

(I-2) 32 O CH₃ H (2) Cl (4) Cl H

(I-2) 33 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 2.11^(a)) 34 O CH₃ H (2) Cl (4) Cl H

(I-2) 35 O CH₃ H (2) Cl (4) Cl H

(I-2) 36 O CH₃ H (2) Cl (4) Cl H

(I-2) 37 O CH₃ H (2) Cl (4) Cl H

(I-2) 38 O CH₃ H (2) Cl (4) Cl H

(I-2) 39 O CH₃ H (2) Cl (4) Cl H

(I-2) 40 O CH₃ H (2) Cl (4) Cl H

(I-2) 41 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.10^(a)) 42 O CH₃ H (2) Cl (4) Cl H

(I-2) 43 O CH₃ H (2) Cl (4) Cl H

(I-2) 44 O CH₃ H (2) Cl (4) Cl H

(I-2) 45 O CH₃ H (2) Cl (4) Cl H

(I-2) 46 O CH₃ H (2) Cl (4) Cl H

(I-2) 47 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.99^(a)) 48 O CH₃ H (2) Cl (4) Cl H

(I-2) 49 O CH₃ H (2) Cl (4) Cl H

(I-2) 50 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 51 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 52 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 53 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 54 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 55 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 56 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 57 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 58 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 59 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 60 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 61 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 62 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 63 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 64 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 65 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 66 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 67 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 68 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 69 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 70 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 71 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 72 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 73 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 74 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 75 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 76 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 77 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 78 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 79 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 80 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 81 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 82 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 83 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 84 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 85 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 86 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 87 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 88 O CH₃ H (4) CF₃ — H

(I-1) 89 O CH₃ H (4) CF₃ — H

(I-1) 90 O C₂H₅ H (4) CF₃ — H

(I-1) 91 O CH₃ H (4) CF₃ — H

(I-1) 92 O CH₃ H (4) CF₃ — H

(I-1) 93 O CH₃ H (4) CF₃ — H

(I-1) 94 O CH₃ H (4) CF₃ — H

(I-1) 95 O C₂H₅ H (4) CF₃ — H

(I-1) 96 O C₂H₅ H (4) CF₃ — H

(I-1) 97 O CH₃ H (4) CF₃ — H

(I-1) 98 O C₂H₅ H (4) CF₃ — H

(I-1) 99 O C₂H₅ H (2) Cl (4) Cl CH₃

(I-2) logP = 1.40^(a)) 100 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.42^(a)) 101 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 2.42^(a)) 102 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 3.30^(a)) 103 O C₂H₅ H (4) CF₃ — CH₃

(I-1) logP = 1.78^(a)) 104 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.25^(a)) 105 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.33^(a)) 106 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.75^(a)) 107 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.50^(a)) 108 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.06^(a)) 109 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 0.72^(a)) 110 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.52^(a)) 111 O C₂H₅ H (2) OCH₃ — H

(I-3) logP = 1.74^(a)) 112 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.82^(a)) 113 O CH₃ H (2) Cl (4) Cl H

(I-2) 114 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 115 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 116 O CH₃

(2) Cl (4) Cl H

(I-2) 117 O C₃H₇-i H (2) Cl (4) Cl H

(I-2) 118 O

H (2) Cl (4) Cl H

(I-2) 119 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 120 O CH₃

(2) Cl (4) Cl H

(I-2) 121 O C₃H₇-i H (2) Cl (4) Cl H

(I-2) 122 O

H (2) Cl (4) Cl H

(I-2) 123 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 124 O CH₃

(2) Cl (4) Cl H

(I-4) 125 O C₃H₇-i H (2) Cl (4) Cl H

(I-2) 126 O

H (2) Cl (4) Cl H

(I-2) 127 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.07^(a)) 128 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.33^(a)) 129 O CH₃ H (2) Cl (4) Cl H

(I-2) 130 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 131 O CH₃ H (2) Cl (4) Cl H

(I-2) 132 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 133 O CH₃ H (2) Cl (4) Cl H

(I-2) 134 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 135 O CH₃

(2) Cl (4) Cl H

(I-2) 136 O C₃H₇-i H (2) Cl (4) Cl H

(I-2) 137 O

H (2) Cl (4) Cl H

(I-2) 138 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 139 O CH₃

(2) Cl (4) Cl H

(I-2) 140 O C₃H₇-i H (2) Cl (4) Cl H

(I-2) 141 O

H (2) Cl (4) Cl H

(I-2) 142 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 143 O CH₃ H (2) Cl (4) Cl H

(I-2) 144 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 145 O CH₃

(2) Cl (4) Cl H

(I-2) 146 O C₃H₇-i H (2) Cl (4) Cl H

(I-2) 147 O

H (2) Cl (4) Cl H

(I-2) 148 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.45^(a)) 149 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.18^(a)) 150 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 151 O CH₃

(2) Cl (4) Cl H

(I-2) 152 O C₃H₇-i H (2) Cl (4) Cl H

(I-2) 153 O

H (2) Cl (4) Cl H

(I-2) 154 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 155 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 156 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.54^(a)) 157 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 158 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 159 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 2.37^(a)) 160 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 161 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.11^(a)) 162 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.38^(a)) 163 S CH₃ H (2) Cl (4) Cl H

(I-2) 164 S C₂H₅ H (2) Cl (4) Cl H

(I-2) 165 O C₂H₅ H (4) CF₃ — H

(I-1) 166 O CH₃ H (2) NO₂ — H

(I-3) 167 O CH₃ H (4) CF₃ — H

(I-1) 168 O C₂H₅ H (2) NO₂ — H

(I-3) 169 O CH₃ H (2) OCH₃ — H

(I-1) 170 O C₂H₅ H (2) OCH₃ — H

(I-1) 171 O C₂H₅ H (2) Cl (4) Cl CH₃

(I-2) logP = 2.88^(a)) 172 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.96^(a)) 173 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.70^(a)) 174 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.20^(a)) 175 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 2.24^(a)) 176 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.39^(a)) 177 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.13^(a)) 178 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.43^(a)) 179 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.72^(a)) 180 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.13^(a)) 181 O C₂H₅ H (2) Cl (4) Cl H

(I-2) logP = 1.63^(a)) 182 O CH₃ H (2) Cl (4) Cl H

(I-2) logP = 1.36^(a)) 183 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) logP = 1.53^(a)) 184 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) logP = 1.34^(a)) 185 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) logP = 1.10^(a)) 186 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) logP = 1.31^(a)) 187 O CH₃ H (2) Cl (4) Cl H

(I-2) 188 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 189 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 190 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 191 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 192 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 193 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 194 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 195 O CH₃ H (2) Cl (4) Cl H

(I-2) 196 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 197 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 198 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 199 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 200 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 201 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 202 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 203 O CH₃ H (2) Cl (4) Cl H

(I-2) 204 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 205 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 206 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 207 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 208 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 209 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 210 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 211 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 212 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 213 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 214 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 215 O CH₃ H (2) Cl (4) Cl H

(I-2) 216 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 217 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 218 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 219 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 220 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 221 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 222 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 223 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 224 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 225 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 226 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 227 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 228 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 229 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 230 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 231 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 232 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 233 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 234 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 235 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 236 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 237 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 238 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 239 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 240 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 241 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 242 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 243 O CH₃ H (2) Cl (4) Cl H

(I-2) 244 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 245 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 246 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 247 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 248 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 249 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 250 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 251 O CH₃ H (2) Cl (4) Cl H

(I-2) 252 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 253 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 254 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 255 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 256 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 257 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 258 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 259 O CH₃ H (2) Cl (4) Cl H

(I-2) 260 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 261 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 262 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 263 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 264 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 265 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 266 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 267 O CH₃ H (2) Cl (4) Cl H

(I-2) 268 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 269 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 270 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 271 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 272 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 273 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 274 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 275 O CH₃ H (2) Cl (4) Cl H

(I-2) 276 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 277 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 278 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 279 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 280 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 281 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 282 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 283 O CH₃ H (2) Cl (4) Cl H

(I-2) 284 O C₂H₅ H (2) Cl (4) Cl H

(I-2) 285 O CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 286 O C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 287 O CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 288 O C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 289 O CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 290 O C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 291 S CH₃ H (2) Cl (4) Cl H

(I-2) 292 S C₂H₅ H (2) Cl (4) Cl H

(I-2) 293 S CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 294 S C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 295 S CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 296 S C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 297 5 CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 298 S C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 299 S CH₃ H (2) Cl (4) Cl H

(I-2) 300 S C₂H₅ H (2) Cl (4) Cl H

(I-2) 301 S CH₃ CH₃ (2) Cl (4) Cl H

(I-2) 302 S C₂H₅ CH₃ (2) Cl (4) Cl H

(I-2) 303 S CH₃ H (2) Cl (4) SO₂CH₃ H

(I-2) 304 S C₂H₅ H (2) Cl (4) SO₂CH₃ H

(I-2) 305 S CH₃ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2) 306 S C₂H₅ CH₃ (2) Cl (4) SO₂CH₃ H

(I-2)

The logP valvues given Table 1 were in accordance with EEC directive79/831 Annex V.A8 HPLC (High Performance Liquid Chromatography) using areversed-phase column (C 18) Temperature: 43° C.

(a) Mobile phases for the determination in the acidic range: 0.1%aqueous phosphoric acid, acetonitrile; linear gradient from 10%acetonitrile to 90% acetonitrile—the corresponding measurement resultsin Table 1 are marked ^(a)).

(b) Mobile phases for the determination in the neutral range: 0.01 molaraqueous phosphate buffer solution, acetonitrile; linear gradient from10% acetonitrile to 90% acetonitrile—the corresponding measurementresults in Table 1 are marked ^(b)).

Calibration was carried out using unbranched alkan-2-ones (having 3 to16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanols).

The lambda max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm.

Starting Materials of the Formula (III) Example (III-1)

A mixture of 11.3 g (32.9 mMol) of methyl2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl)-carbonyl]-amino]-benzoate,50 ml of water, 50 ml of tetrahydrofuran and 1.3 g of sodium hydroxideis stirred at room temperature (about 20° C.) for 18 hours and thenconcentrated under reduced pressure to about half its original volume.The mixture is then shaken with diethyl ether, the organic phase isseparated off (and discarded) and the aqueous phase is acidified withconc. hydrochloric acid. The resulting crystalline product is isolatedby filtration with suction.

This gives 9.1 g (81.5% of theory) of2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl)-carbonyl]-amino]-benzoicacid.

logP (pH=2.3): 1.35.

Analogously to Example (III-1), it is also possible to prepare, forexample, the compounds of the general formula (III) listed in Table 2below.

TABLE 2 (III)

Examples of the compounds of the formula (III) Ex.-No. (position) R³(position) R⁴ (position)

Physical Data III-2 (2) Cl (4) Cl (3)

logP = 1.17^(a)) III-3 (2) Cl (4) Cl (3)

III-4 (2) Cl (4) Cl (3)

logP = 1.58^(a)) III-5 (2) Cl (4) Cl (3)

III-6 (2) Cl (4) Cl (3)

logP = 0.78^(a)) III-7 (2) Cl (4) Cl (3)

logP = 1.05^(a)) III-8 (2) Cl (4) Cl (3)

III-9 (4) CF₃ — (2)

logP = 2.43^(a)) III-10 (4) CF₃ — (2)

logP = 2.13^(a)) III-11 (4) CF₃ — (2)

III-12 (4) CF₃ — (2)

III-13 (4) CF₃ — (2)

III-14 (4) CF₃ — (2)

III-15 (4) CF₃ — (2)

Starting Materials of the Formula (IIIa) Example (IIIa-1)

A mixture of 12.3 g (50 mMol) of methyl2,4-dichloro-3-isocyanato-benzoate, 5.0 g (50 mmol) of1-methyl-2-oxo-imidazolidine, a few drops of triethylamine and 100 ml ofacetonitrile is stirred at room temperature (about 20° C.) for 18 hoursand then concentrated under reduced pressure. The residue is thendigested with diethyl ether and the crystalline product is isolated byfiltration with suction.

This gives 11.4 g (60% of theory) of methyl2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl)-carbonyl]-amino]-benzoate.

logP (pH=2.3): 1.94.

Analogously to Example (IIIa-1) it is also possible to prepare, forexample, the compounds of the general formula (IIIa) listed in Table 3below.

TABLE 3 (IIIa)

Examples of the compounds of the formula (IIIa) Ex.-No. R (position) R³(position) R⁴ (position)

Physical Data IIIa-2 CH₃ (2) Cl (4) Cl (3)

IIla-3 CH₃ (2) Cl (4) Cl (3)

IIIa-4 CH₃ (2) Cl (4) Cl (3)

IIIa-5 CH₃ (2) Cl (4) Cl (3)

IIIa-6 CH₃ (2) Cl (4) Cl (3)

logP = 1.34^(a)) IIIa-7 CH₃ (2) Cl (4) Cl (3)

logP = 1.64^(a)) IIIa-8 CH₃ (2) Cl (4) Cl (3)

logP = 0.50^(a)) IIIa-9 CH₃ (4) CF₃ — (2)

logP = 3.35^(a)) IIIa-10 CH₃ (4) CF₃ — (2)

logP = 2.76^(a)) IIIa-11 CH₃ (4) CF₃ — (2)

IIIa-12 CH₃ (4) CF₃ — (2)

IIIa-13 CH₃ (4) CF₃ — (2)

IIIa-14 CH₃ (4) CF₃ — (2)

IIIa-15 CH₃ (4) CF₃ — (2)

IIIa-16 CH₃ (2) Cl (4) Cl (3)

Use Examples Example A

Pre-emergence Test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight ofalkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours, thesoil is sprayed with the preparation of active compound such that theparticular amount of active compound desired is applied per unit area.The concentration of active compound in the spray liquor is chosen suchthat the particular amount of active compound desired is applied in 1000liters of water per hectare.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control. Thefigures denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

In this test, for example, the compounds of Preparation Examples 1, 2,3, 4, 5 and 6 exhibit strong activity against weeds, and some aretolerated well by crop plants, such as, for example, maize.

Example B

Post-emergence Test

Solvent: 5 parts by weight of acetone Emulsifier: 1 by weight ofalkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants of a height of 5-15 cm are sprayed with the preparation ofactive compound such that the particular amounts of active compounddesired are applied per unit area. The concentration of the spray liquoris chosen such that the particular amounts of active compound desiredare applied in 1000 l of water/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

In this test, for example, the compounds of Preparation Examples 1, 2,and 5 exhibit strong activity against weeds.

1. A compound of formula (I)

including any tautomeric forms thereof or a salt of a compound offormula (I) including any tautomeric forms thereof, in which Qrepresents O (oxygen) or S (sulphur), R¹ represents methyl, ethyl, or n-or i-propyl, R² represents hydrogen, methyl, ethyl, methoxycarbonyl,ethoxycarbonyl, methylthio, or ethylthio, R³ and R⁴ independently of oneanother represent hydrogen, nitro, cyano, fluorine, chlorine, bromine,methyl, ethyl, difluoromethyl, trifluoromethyl, dichloro -methyl,trichloromethyl, methoxymethyl, methylthiomethyl, methylsulphinyl-methyl, methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy,trifluoro -methoxy, methylthio, ethylthio, methylsulphinyl,ethylsulphinyl, methyl -sulphonyl, ethylsulphonyl, ordimethylaminosulphonyl, R⁵ represents hydrogen; represents methyl,ethyl, or n- or i-propyl; represents methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, or ethylsulphonyl; represents optionally fluorine-and/or chlorine-substituted propenyl, butenyl, propynyl, or butynyl; orrepresents cyclopropyl, Y represents hydrogen; represents optionallycyano-, fluorine-, methoxy-, ethoxy-, methoxycarbonyl-, orethoxycarbonyl-substituted methyl or ethyl; represents optionallyfluorine- and/or chlorine-substituted methylsulphonyl or ethylsuiphonyl;represents optionally cyano-, fluorine-, chlorine-, methoxy-, orethoxy-substituted acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl,methylaminocarbonyl, or ethylaminocarbonyl; represents dimethylamino-carbonyl; represents optionally fluorine-, chlorine-, orbromine-substituted propenyl, propenylcarbonyl, propynyl, orpropynylcarbonyl; represents optionally cyano-, fluorine-, chlorine- ormethyl-substituted cyclopropyl -carbonyl, cyclobutylcarbonyl,cyclopentylcarbonyl, cyclohexylcarbonyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl, or cyclohexylmethyl; or representsoptionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy-, ortrifluoro -methoxy-substituted phenyl, phenylsulphonyl, phenylcarbonyl,phenylmethyl, phenylmethylsulphonyl, phenylmethylcarbonyl, orphenylcarbonylmethyl and Z represents cyanoamino, or hydrazino;represents methoxyamino, ethoxyamino, n- or i-propoxyamino,methylhydrazino, ethylhydrazino, n- or i-propylhydrazino, or n-, i-, s-,or t-butylhydrazino; represents N-methyl -methoxyamino ordimethylhydrazino; represents optionally fluorine- and/orchlorine-substituted propenyloxy, butenyloxy, propenylthio, butenylthio,propenylamino, butenylamino, propenyloxyamino, butenyloxyamino,propynyloxy, butynyloxy, propynylamino, or butynylamino; representsoptionally cyano-, fluorine-, chlorine- or methyl-substitutedcyclopropyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclopentyloxy,cyclohexyloxy, cyclopropylamino, cyclopentylamino, cyclohexylamino,cyclohexylhydrazino, cyclopropylmethoxy, cyclopentylmethoxy,cyclohexylmethoxy, cyclopropyl -methylamino, cyclopentylmethylamino, orcyclohexylmethylamino; represents optionally nitro-, cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s-, ort-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-, ethoxy-carbonyl-, or n- or i-propoxycarbonyl-substituted phenyl,phenylcarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylamino,phenylhydrazino, phenylmethoxy, phenylethoxy, phenylmethylthio,phenylethylthio, phenylmethylamino, or phenylethylamino; or representsoptionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, n- or i-propyl-, n-, i-, s-, or t-butyl-, cyclopropyl-,cyclobutyl-, cyclopentyl-, cyclohexyl-, difluoromethyl-,trifluoromethyl-, dichloromethyl-, trichloromethyl-,chlorodifluoromethyl-, fluorodichioromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-,ethylthio-, n- or i-propylthio-, difluoromethyl -thio-,trifluoromethyithio-, methoxycarbonyl-, ethoxycarbonyl-, or n- or i-propoxycarbonyl-substituted monocyclic or bicyclic heterocyclyl,heterocyclyl -oxy, heterocyclylamino, heterocyclylalkyl,heterocyclylalkoxy, or heterocyclyl -alkylamino selected from the groupconsisting of furyl, furyloxy, furylamino, furylmethoxy,furylmethylamino, tetrahydrofuryl, tetrahydrofuryloxy,tetrahydrofurylamino, tetrahydrofurylmethoxy,tetrahydrofurylmethylamino, dioxolanyl, dioxolanylmethoxy,dioxolanylmethylamino, thienyl, thienylamino, thienylmethylamino,dithiolanyl, dithiolanylmethoxy, dithiolanylmethylamino, pyrrolidinyl,pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrazolyl,pyrazolyloxy, pyrazolylamino, imidazolyl, imidazolinyl, 2-oxo-1,3-diaza-cyclopentyl, oxazolyl, oxazolylmethyl, dihydrooxazolyl (oxazolinyl),tetrahydro -oxazolyl (oxazolidinyl), isoxazolyl, dihydroisoxazolyl(isoxazolinyl), tetrahydro -isoxazolyl (isoxazolidinyl), thiazolyl,dihydrothiazolyl (thiazolinyl), tetrahydro -thiazolyl (thiazolidinyl),oxothiazolidinyl, cyanoiminothiazolidinyl, oxotriazolinyl,oxotetrazolinyl, dioxanyl, dioxanylmethoxy, dioxanylmethylamino,dithianyl, dithianylmethoxy, dithianylmethylamino, triazolylamino,piperidinyl, piperidinylamino, oxopiperidinyl,2-oxo-1,3-diaza-cyclohexyl, 2-oxo-1-aza -cycloheptyl,2-oxo-1,3-diaza-cycloheptyl, morpholinyl, oxomorpholinyl,morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino,pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, and pyrimidinylmethoxy.2. A process for preparing a compound of formula (I) according to claim1 comprising (a) reacting a pyrazole of formula (II)

in which R¹, R², and Y are as defined for formula (I) in claim 1, with asubstituted benzoic acid of formula (III)

in which Q, R³, R⁴, R⁵ and Z are as defined for formula (I) in claim 1,or a reactive derivative thereof, optionally in the presence of adehydrating agent, optionally in the presence of one or more reactionauxiliaries, and optionally in the presence of one or more diluents, or(b) reacting a substituted benzoylpyrazole of formula (Ia)

in which Q, R¹, R², R³, R⁴, R⁵ and Z are as defined for formula (I) inclaim 1, with a compound of formula (IV)X—Y  (IV) in which Y is as defined for formula (I) in claim 1, exceptfor excluding hydrogen, and X represents halogen, or optionally with acorresponding acid anhydride, isocyanate, or isothiocyanate, optionallyin the presence of one or more reaction auxiliaries and optionally inthe presence of one or more diluents.
 3. A process according to claim 2additionally comprising (i) subjecting the resulting compound of formula(I) to electrophilic or nucleophilic substitution reactions and/oroxidation or reduction reactions to interconvert substituents within themeaning of formula (I) and/or (ii) converting the resulting compound offormula (I) into a salt thereof.
 4. A herbicidal composition comprisingone or more compounds of formula (I) according to claim 1 and one ormore extenders.
 5. A method for controlling undesirable plantscomprising allowing one or more compounds according to claim 1 to act onan undesirable plant and/or its habitat.
 6. A compound of formula (I-a)

in which Q represents O (oxygen) or S (sulphur), R¹ representsoptionally substituted alkyl, alkenyl, alkynyl, or cycloalkyl, R²represents hydrogen, cyano, carbamoyl, thiocarbamoyl, or halogen; orrepresents optionally substituted alkyl, alkoxy, alkylthio,alkoxycarbonyl, or cycloalkyl, R³ and R⁴ independently of one anotherrepresent hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl,halogen, or optionally substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino,dialkyl-aminocarbonyl, or dialkylaminosulphonyl, R⁵ represents hydrogen;represents optionally substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkenyl, alkynyl, cycloalkyl,cycloalkylalkyl, aryl, arylthio, arylsulphinyl, arylsulphonyl, orarylalkyl; or represents the group —C(Q)-Z, and Z represents cyanoamino,nitroamino, hydroxyamino, or hydrazino; represents alkylthio; orrepresents optionally substituted alkylcarbonyl, alkoxycarbonyl,alkoxyamino, alkylhydrazino, alkylcarbonyl -hydrazino,alkoxycarbonylhydrazino, alkylsulphonylhydrazino, N-alkyl -alkoxyamino,dialkylhydrazino, alkenyloxy, alkenylamino, alkenyloxyamino, alkynyloxy,alkynylamino, cycloalkyl, cycloalkyloxy, cycloalkylamino,cycloalkylhydrazino, cycloalkylalkoxy, cycloalkylalkylamino, aryl,arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, arylamino,arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio, arylalkylamino,heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, thegroup —N═(heterocyclyl), heterocyclylalkoxy, heterocyclylalkylthia, orheterocyclylalkylamino.
 7. A method for controlling undesirable plantscomprising allowing one or more compositions according to claim 4 to acton an undesirable plant and/or its habitat.
 8. A compound of the formula(I-2)

in which Q represents O (oxygen), R¹ represents optionally substitutedalkyl, R² represents hydrogen, R³ and R⁴ independently of one anotherrepresent halogen, R⁵ represents hydrogen, and Z representsalkoxy-substituted alkylamino; or represents optionally methyl-, ethyl-,n- or i-propyl, or n-, i-, s- or t-butyl-substituted heterocyclylselected from the group consisting of pyrrolidinyl, pyrrolidinyl -amino,oxopyrrolidinyl, pyrrolyl, imidazolinyl, 2-oxo-1,3-diazacyclopentyl,dihydrooxazolyl (oxazolinyl), tetrahydrooxazolyl (oxazolidinyl), dihydro-isoxazolyl (isoxazolinyl), tetrahydroisoxazolyl (isoxazolidinyl),tetrahydro-(2H) -1,2-oxazin-2-yl, piperidinyl, oxopiperidinyl,2-oxo-1,3-diaza-cyclohexyl, 2-oxo -1-aza-cycloheptyl,2-oxo-1,3-diaza-cycloheptyl, morpholinyl, oxomorpholinyl, orpiperazinyl.